


baby you're a rich man.

by katarama



Series: Tumblr Ficlets [18]
Category: Teen Wolf (TV)
Genre: Alcohol, BDSM, Butt Plugs, M/M, Rich Derek Hale, Sex Toys, Sugar Daddy
Language: English
Status: Completed
Published: 2015-11-22
Updated: 2015-11-22
Packaged: 2018-05-02 21:58:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,323
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5265215
Author URL: https://archiveofourown.org/users/katarama/pseuds/katarama
Summary: <blockquote class="userstuff">
              <p>The boy himself is probably the most interesting part of the night so far.  Derek can’t remember having seen him before, at any events like these, and fresh blood is interesting in and of itself.  Derek didn’t see who he came in with, but Derek watches him go back and forth between Lydia and one of the men pushing his mid-fifties.  He walks around like he was made for events like this in a way Derek isn’t, all cheekbones and smirks and gazes through his eyelashes.  Derek remembers with particular vividness the briefest moment when his eyes met the boy’s clear blue ones from across the room, remembers the cocky grin that broke across the boy’s face.</p><p>Derek notices him more after that.</p>
            </blockquote>





	baby you're a rich man.

Derek twirls his drink, listens to the ice clink against the glass.  He doesn’t actually want to finish it; he’s never liked the taste of whiskey, and he only ever gets it because it gets him tipsy quickly.  He doesn’t need it, but it’s going to make the night easier on him, help him drop some of the tension he’s holding tight in his shoulders.  

The room is too crowded for his tastes, too full of people he knows vaguely, could recognize in a lineup as part of the scene, but doesn’t know a single personal thing about.  He’s always been happier with his books and his sisters than with large groups of people.  He’s never quite gotten the hang of small talk, not like his mom, and he can’t emulate the tricky nuances of Peter’s schmoozing.  Laura has always taken the bold approach, surrounding herself with brash, young friends who spend most of their time out.  Derek had followed her lead for a while, until he met Kate, skin soft but smile sharp.  

Derek cut out of that lifestyle just in time to watch Kate self-destruct, and now, he’s more careful.  He usually comes to these events alone.  It’s far from ideal, and he feels like sometimes these events can be reduced to him drinking and wallowing in his awkwardness.  

“They’re a necessary evil,” his mother had always told him, though.  “Something you just have to do.”  And if there’s anything Derek understands by now, it’s that even being the middle child does not let him escape his social obligations free from guilt.

Cora’s there with him this time, but not for business purposes.  She’s been picking fights with Lydia Martin all night, her flirting style as aggressive as it is unsubtle.  It verges on inappropriate behavior when surrounded by suits and cocktail dresses and watchful eyes, but Derek doesn’t begrudge Cora her her fun, as long as Lydia isn’t bothered.  

Besides, watching Cora’s hackles rise every time the short boy in the grey suit comes circling back around to Lydia is admittedly more interesting than Derek’s discussions, which, at this point in the night, are swerving towards profit margins.

The boy himself is probably the most interesting part of the night so far.  Derek can’t remember having seen him before, at any events like these, and fresh blood is interesting in and of itself.  Derek didn’t see who he came in with, but Derek watches him go back and forth between Lydia and one of the men pushing his mid-fifties.  He walks around like he was made for events like this in a way Derek isn’t, all cheekbones and smirks and gazes through his eyelashes.  

The night blurs by, a mess of stilted conversation that gets easier but less coherent the drunker the people around Derek get.  Derek walks out that night with little recollection of what he said, but he remembers with particular vividness the briefest moment when his eyes met the boy’s clear blue ones from across the room, remembers the cocky grin that broke across the boy’s face.

Derek notices him more after that.

He sees him a few more times, all with the same man.  The boy hangs off his arm, is attentive but never very affectionate.  Derek can’t tell what the story is there, though he spends a great deal of time trying to figure out.  He wonders if it’s a gold digger situation, an upstart attaching himself to an older gentleman hoping to make enough bank from the relationship to linger in the social circles until the money’s all blown.  Derek isn’t too naive to think it doesn’t happen.  Ennis is still sore about Jennifer Blake, who he had gone as far as marrying before he realized he was being used; Derek thinks it’s more his fault than Jennifer’s, because Ennis was always loud about how traditionalism was better and prenups were inappropriate.  It made everyone a little less sympathetic when he gave Jennifer half his estate for her to enjoy when she divorced him and ran off with Kali.

Derek figures that it’s more of the same with this guy until he drops off the radar.  His older boyfriend stops showing up at parties not long after and starts showing up in the news, charges of fraud.  Derek gets used to searching for them both, scanning the room at every major networking event for a well-fitted suit and hair cut short and blue eyes.  But Derek can’t find him, and he wonders where he went.  Even though Derek’s never talked to him, they have their own quiet little interactions, passing each other on the way to the bar or glancing across the room at each other.  The parties are always more interesting for him being there.

When Derek finally sees him again, it’s two months later.  His hair has grown longer, and he’s with someone new.  And then a week later, he’s with Scott McCall, winking at Derek across the room.  Stiles Stilinski, a new money friend of Scott’s with a reputation for being too talkative, catches Derek looking, and he’s practically bursting at the seams to share all the information he has.  In one sense, it’s a relief; it’s too late for Derek to ask anyone else, except maybe Lydia, and Derek is curious enough that Stiles’ gossip is something he actually cares about.

“Jackson Whittemore,” Stiles informs him.  The name prickles in the back of Derek’s head.  He know he’s heard it before, though he doesn’t know where, and he’s glad when Stiles continues on unprompted.  “Daddy’s a bigshot attorney, his family’s loaded.  He got himself cut off fucking around in college, got a couple of DUIs and took too long shape up.  It was everywhere in the tabloids.”

“I quit reading the tabloids a long time ago,” Derek says flatly, but Stiles is too puffed up to be bothered.  Derek doesn’t understand why, thinks that’s the extent of the drama, until Stiles opens his mouth again, practically tripping over himself to get the words out.

“He’s a sugar baby.  Scott agreed to bring him out for the night to help him look for someone new.  He switches between rich and handsome, and the last guy was disgustingly loaded.”

“So he’s looking for handsome.” Jackson glances Derek’s way, smiles coyly.  His shirt is blue, matching his eyes perfectly.  Earlier, Derek swears he saw freckles dotting his cheeks.  Jackson is fit, and he’s never been shy about paying Derek attention.

“Go buy him a drink,” Stiles says.  “Give him your business card, or something.  He’s easy, get him before someone else snaps him up.”

Derek can’t shake Stiles’ words for the rest of the night.  He doesn’t act right away, though he’s thinking about it.  He knows it would be easy to walk right up to Jackson, to treat it like a business deal, to ask for details and to get what he wants.  But he feels awkward and uncertain, the lines blurred between what exactly counts as business and pleasure in these kinds of circumstances.  So gets himself another drink at the bar and finds himself a seat.  

It doesn’t take long before he has company.

“Stiles told me you were interested.”

Derek glances up, sees Jackson standing over him.  His lips are pink and his eyes are blue, and he looks like he’s definitely gotten some sun.  Derek wants to put his mouth on every single freckle dotting his cheeks.  

“Stiles has a big mouth.”

“Horrible gag reflex, though,” Jackson says, and Derek chokes on his drink.  Jackson laughs, just edging on too sharp, and Derek can see it, more clearly than ever, the boy who grew up in this world, who grew his edges rough and his face pretty.  “Are you interested?”

“I’ve never done this before,” Derek admits.  That doesn’t seem to bother Jackson, though; if anything, it makes him more interested.  If Derek knows anything by now, he knows that means he needs to do some poking around before agreeing to anything.

“It’s not hard,” Jackson says.  “I get an allowance and gifts, and you get my company, however you want it.”

“I’ll think about it,” Derek promises.  He already knows he’ll say yes, feels it in his gut when Jackson feels his way down Derek’s thigh to tuck his number into Derek’s suit pants.  Derek still waits three days to call, and it only manages that long through an extreme exercise of self-restraint.

* * *

 

When Jackson said Derek could have his company however he wanted it, Derek assumed Jackson was only implying bedroom activities.  But Derek does some reading up and realizes he’s wrong, and he takes full advantage of it.  He takes Jackson out at first in the places Jackson would expect, five star dinners where Jackson can show off his new watch or his new dress shirt.  Derek gets old of that quickly, though, and subjects Jackson to dinner at his favorite diner.  Seeing how different Jackson is when he’s not not surrounded by people he’s trying to get something from is an interesting experience.  Derek realizes quickly that Jackson is far from smooth; at best, he’s bratty and relatively sullen, complaining frequently about Derek’s choices.  It grates on Derek’s nerves, at first; even the little challenges feel bigger when launched from Jackson’s mouth.

It also feels real, though, and Derek realizes quickly that, though Jackson’s company isn’t quite what he expected, there are some definite benefits.  He gets to gripe and tease just as much as Jackson does, and it gives him the chance to get some of his tension out in a way he only ever gets to with his sisters, anymore.  That, if nothing else, would be worth shelling out for the allowances.  

But once they start having sex, it becomes even more fun, because learning Jackson in bed feels like learning Jackson all over.  Picking out gifts for Jackson becomes one of the best parts of their arrangement, a small vibe that Derek knows would look good inside Jackson, or a ball gag Jackson had put on his Amazon wishlist.  Jackson goes to events with Derek, and half the time, he’s plugged up, squirming and losing his focus because he’s hard in his brand new suit pants that Derek bought for him.  Derek doesn’t break for a moment, even when Jackson tries to whisper in Derek’s ear and hook Derek by the elbow to drag him into the bathroom.

“Be patient,” Derek tells him firmly, and Jackson shivers and whines, but doesn’t disobey.

They grow into each other.  Jackson is never romantic, but he can be soft, and Derek drinks in all of those moments that Jackson lets him have.  They agree to tell Laura and Cora that Jackson’s his boyfriend, because, the longer they’re together, the more he fills that role.  Derek sometimes thinks back to what he read on the websites with information about common courtesy and rules for sugar daddies, and he wonders if lines have been crossed somewhere.  It doesn’t feel like anything transactional to Derek; it feels like they’re dating in earnest, even though it comes with deposits to Jackson’s bank account.  Jackson isn’t looking anymore, and his belongings have started trickling into Derek’s place, suits finding their home in the closet and underwear and tennis shoes migrating to under Derek’s bed.

But the moments that feel the softest, the most like actual boyfriend moments, come when Jackson stays the night.

Derek wakes up slowly to a stirring in his gut, to his gorgeous boy’s mouth on his cock.  The orgasm comes quick but easy, making Derek sink into the softness of his mattress and want to cling there, to bring Jackson, with his half-lidded, sleepy eyes, close to his chest and keep him there with him.  They kiss, Jackson grabbing a mint from the bedside table and passing it into Derek’s mouth with his tongue, because kissing Derek while he has morning breath is something Jackson adamantly refuses to do.  

Derek opens Jackson up in the shower with his fingers, plugs him up and makes coffee.  Jackson settles himself under the table, sucks Derek down as deep as he can while Derek reads the morning newspaper, Derek’s toes curling as his eyes skim over the same sentence again and again.  Derek puts his hand on Jackson’s head and pulls at his soft, damp hair, pushes Jackson down deeper on his cock until even Jackson’s moans are muffled.  Jackson’s noises alone could distract Derek from his newspaper, the sloppy pop of Jackson’s lips when Derek lets him pull up for air and the whimpers when Derek tugs just a bit too hard, but Derek loves hearing them, loves knowing that Jackson feels so needy and good that he can’t keep them in.

When Jackson’s licked the come from his lips, Derek turns the vibe on on Jackson’s plug, gets his big warm hands around Jackson’s dick until he’s spurting come all over his chest, onto his abs and the neatly trimmed patch of body hair he’s growing between his tits.  When Jackson’s loose, Derek pulls him onto his lap, eases the plug out and feeds him bites of toast.  Morning breath kisses are off-limits, and orange juice and coffee kisses aren’t, though Jackson always grumbles about them afterwards.  

They’re mornings when Derek doesn’t have to wake up alone, when he gets to share the little bits of daily life with someone else.  He never would’ve thought that person would be Jackson, never in a million years would’ve imagined Jackson happily going down on his knees for Derek, hungry for him and so blissed out in the aftermath that the softness Derek enjoys is something Jackson needs.  

When Jackson is more awake, it’s back to normal, the two of them trading barbs and reminding each other just how quick they both are to mild threats of violence.  

As long as Jackson wants to stay, Derek will keep him.

**Author's Note:**

> On tumblr [here](sleepy-skittles.tumblr.com)!


End file.
